A lake surrounded by autumn-colored trees reflecting on the water.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Middletown cottages

Exterior

1. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (6 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$351 nightly
The price is $397
Sep 20 - Sep 21
Total with taxes and fees
Hello Small Stone
Living area

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (14 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$281 nightly
The price is $293
Sep 24 - Sep 25
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
House (1 Bedroom) | Interior

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$304 nightly
The price is $344
Sep 20 - Sep 21
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
Property grounds

4. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.4 out of 10, Exceptional, (3 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
$192 nightly
The price is $216
Sep 21 - Sep 22
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

5. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (18 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
$223 nightly
The price is $226
Oct 5 - Oct 6
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Exterior

6. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (10 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
$364 nightly
The price is $401
Sep 24 - Sep 25
Total with taxes and fees
Cozy Cottage w/ Hot Tub! — Family Friendly
Terrace/patio

7. Cozy Cottage with Woodstock Scavenger Hunt

Cozy Cottage with Woodstock Scavenger Hunt
Mongaup Valley
10.0 out of 10, Exceptional, (6 reviews)
"Great little cottage close to Bethel Woods."
United States
Erin
$247 nightly
The price is $278
Sep 30 - Oct 1
Total with taxes and fees
Cozy Cottage with Woodstock Scavenger Hunt
Property grounds

8. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (145 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Sep 21 - Sep 22
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Room

9. Private Pool House - Pool · Jacuzzi · Fireplace

Private Pool House - Pool · Jacuzzi · Fireplace
Pine Bush
$429 nightly
The price is $480
Sep 21 - Sep 22
Total with taxes and fees
Private Pool House - Pool · Jacuzzi · Fireplace
Outdoor dining

10. Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
9.0 out of 10, Wonderful, (4 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Sep 21 - Sep 22
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"It was inviting and clean. The staff was nice."
Valerie 1-night trip
Posted 11 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Find out more about Middletown

Middletown Cottages information

Number of reviews
206
Accommodation
136 Cottages
Lowest Price
$216
Highest Price
$480

Frequently asked questions

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What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.

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